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20151201150152.0 |
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cr unu|||||||| |
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100428s2010 txu sbm 000 0 eng d |
| 035 |
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|a (OCoLC)ocn609908111
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| 035 |
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|a (OCoLC)609908111
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| 035 |
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|a (TxCM)http://hdl.handle.net/1969.1/ETD-TAMU-3121
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| 040 |
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|a TXA
|c TXA
|d UtOrBLW
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| 049 |
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|a TXAM
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| 099 |
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|a 2008
|a Dissertation
|a 1969.1/ETD-TAMU-3121
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| 100 |
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|a Cho, Sung Wook.
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| 245 |
1 |
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|a Total syntheses of [Beta]-lactone containing natural products :
|b I. total synthesis of belactosin C II. synthetic studies toward spongiolactone /
|c by Sung Wook Cho.
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| 264 |
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1 |
|a [College Station, Tex.] :
|b [Texas A&M University],
|c [2010]
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| 300 |
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|a 1 online resource.
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| 336 |
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|a text
|b txt
|2 rdacontent
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| 337 |
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|a computer
|b c
|2 rdamedia
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| 338 |
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|a online resource
|b cr
|2 rdacarrier
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| 500 |
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|a "Major Subject: Chemistry"
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| 500 |
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|a Title from author supplied metadata (automated record created 2010-03-12 12:08:51).
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| 502 |
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|b Doctor of Philosophy
|c Texas A&M University
|d 2008
|o http://hdl.handle.net/1969.1/ETD-TAMU-3121
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| 504 |
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|a Includes bibliographical references.
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| 516 |
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|a Text (Dissertation)
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|a The recently isolated bacterial metabolites, belactosins A-C from a fermentation broth of Streptomyces sp. UCK14, uniquely contain a B-lactone dipeptide motif and exhibit anticancer activities. The enantioselective synthesis of (-)-belactosin C and derivatives was accomplished in a concise manner employing the tandem, Mukaiyama aldol-lactonizaton (TMAL) process and test their bioactivities. . One approach involved a distal double diastereoselective TMAL reaction with a dipeptide glyoxamide, whereas a second approach involved amide coupling of a dipeptide with a B-lactone carboxylic acid, obtained via the TMAL process employing a chiral silyl ketene acetal. Enzymatic assays showed that the belactosins act as the dual inhibitors of the proteasome and the thioesterase domain of fatty acid synthase. Spongiolactone which uniquely contains a cyclopentyl-fused B-lactone was isolated in 1986 from Spongi-onellagracilis No biological activity have been reported for this compound; however, the acylating potential of the resident B-lactone warrants screening for potential activity. After many setbacks in the synthesis of spongiolactone, significant progress has been made. Importantly, NCAL process also enabled a concise construction of [3.2.0]-bicyclo B-lactone, which is the key structure in the spongiolactone synthesis and only a few steps remained to complete the synthesis.
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|a Electronic resource.
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|a Major chemistry.
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|a TMAL
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|a NCAL
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|a Synthesis
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|a β
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|a -Lactone
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| 653 |
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|a Spongiolactone
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| 653 |
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|a Belactosin C
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| 700 |
1 |
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|a Gabbai, Francois P.,
|e thesis advisor.
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| 700 |
1 |
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|a Romo, Daniel,
|e thesis advisor.
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| 856 |
4 |
0 |
|u http://hdl.handle.net/1969.1/ETD-TAMU-3121
|z Link to OAK Trust copy
|t 0
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| 948 |
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|a cataloged
|b h
|c 2010/4/28
|d c
|e jgreene
|f 4:40:38 pm
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| 994 |
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|a C0
|b TXA
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|a MARS
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| 999 |
f |
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|s 59f15c30-3666-3f9a-b256-78b6c7d8b6e8
|i b476a423-60fa-3244-aee1-db926b5989bf
|t 0
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| 952 |
f |
f |
|a Texas A&M University
|b College Station
|c Electronic Resources
|s www_evans
|d Available Online
|t 0
|e 2008 Dissertation 1969.1/ETD-TAMU-3121
|h Other scheme
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| 998 |
f |
f |
|a 2008 Dissertation 1969.1/ETD-TAMU-3121
|t 0
|l Available Online
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